Citric Acid → t-Butyl 2-methoxy-6-(2-oxopyrrolidin-1-yl)pyridine-4-carboxylate

HRID 1612468Notes

Reaction equation

HRID 1612468 reaction equation
Br[CH2:2][CH2:3][CH2:4][C:5]([NH:7][C:8]1[CH:13]=[C:12]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH:11]=[C:10]([O:21][CH3:22])[N:9]=1)=[O:6].C1CCN2C(=NCCC2)CC1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>O1CCOCC1>[CH3:22][O:21][C:10]1[CH:11]=[C:12]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH:13]=[C:8]([N:7]2[CH2:2][CH2:3][CH2:4][C:5]2=[O:6])[N:9]=1

Participants

5

Reactant 3

HCID 311Citric AcidHCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene2×HCID 22253030t-Butyl 2-(4-bromobutyramido)-6-methoxypyridine-4-carboxylate

Product 1

HCID 22252983t-Butyl 2-methoxy-6-(2-oxopyrrolidin-1-yl)pyridine-4-carboxylateYield 74.7%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

t-Butyl 2-(4-bromobutyramido)-6-methoxypyridine-4-carboxylate (D56) (0.47 g) was dissolved in dioxan and treated with DBU (0.31 mL; 1 eq.). After stirring for 0.5 h, further DBU (0.31 mL; 1 eq.) was added. Stirring was continued for 2 h and the mixture was poured into citric acid solution (10% aq.) and extracted twice with ethyl acetate. The combined extracts were washed with aq. bicarbonate, water and brine, dried (MgSO4) and evaporated, giving the title compound (D57) as a beige solid (0.275 g).

Workup

  1. stirringStirring
  2. waitwas continued for 2 h
  3. extractionextracted twice with ethyl acetate
  4. washThe combined extracts were washed with aq. bicarbonate, water and brine
  5. dry with materialdried (MgSO4)
  6. customevaporated

Sources & evidence

ORD record
ord-c5770a83eb4146ecabe8c1a63dddbe2a
Source dataset
uspto-grants-2006_01
Patent number
US06992103B2

Reaction notes

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